Received 1 August 2013
In the title compound, C24H18N2O5S, the S atom has a distorted tetrahedral configuration, with bond angles varying from 105.11 (7) to 119.98 (8)°. As a result of the electron-withdrawing character of the phenylsulfonyl group, the N-Csp2 bond lengths [1.414 (2) and 1.413 (2) Å] are slightly longer than the reported value of 1.355 (14) Å for N atoms with a planar configuration. The indole moiety is essentially planar, with a maximum deviation of 0.0177 (14) Å for the N atom. The phenyl ring of the sulfonyl substituent makes a dihedral angle of 85.70 (7)° with the mean plane of the indole moiety. The molecular structure features intramolecular C-HO hydrogen bonds, which generate S(6) and S(12) ring motifs. In the crystal, adjacent molecules are linked via C-HO hydrogen bonds, forming infinite C(7) chains running along the a-axis direction. The crystal packing also features C-H interactions, which form a three-dimensional structure.
For the biological activity of Indole derivatives, see: Rodriguez et al. (1985); Chai et al. (2006); Olgen & Coban (2003). For related crystal structures, see: Karthikeyan et al. (2011, 2012). For related bond distances and bond-angle geometries and distortions, see: Allen (1981); Allen et al. (1987). For graph-set notation, see: Bernstein et al. (1995). For the Thorpe-Ingold effect, see: Bassindale (1984).
Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2631 ).
The authors thank Mr T. Srinivasan and Dr D. Velmurugan, The Head, CAS in Crystallography and Biophysics, University of Madras, Chennai, India, for the data collection.
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